Modern-electronic mail systems employ an out of office auto-reply feature for answering email or other messaging when a user is not available to answer a message, such as when a user is on vacation or on a business trip. Typically, when a user knows he is going to be unavailable, the user activates the out of office auto-reply feature, which causes it to generate a preconfigured message to other parties who write to the user during the period of unavailability. However, users often forget to activate the out of office auto-reply feature when they go on vacation and deactivate it when they return.